Ethylene Glycol → N-(1-Adamantylmethyl)-5-chloro-2-(2-hydroxyethoxy)isonicotinamide

HRID 1247601Notes

Reaction equation

[H-].[Na+].[CH2:3]([OH:6])[CH2:4][OH:5].[C:7]12([CH2:17][NH:18][C:19](=[O:28])[C:20]3[C:25]([Cl:26])=[CH:24][N:23]=[C:22](Br)[CH:21]=3)[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[CH2:8]1)[CH2:14]2>CN1CCCC1=O>[C:7]12([CH2:17][NH:18][C:19](=[O:28])[C:20]3[C:25]([Cl:26])=[CH:24][N:23]=[C:22]([O:5][CH2:4][CH2:3][OH:6])[CH:21]=3)[CH2:8][CH:9]3[CH2:10][CH:11]([CH2:12][CH:13]([CH2:15]3)[CH2:14]1)[CH2:16]2

Participants

Conditions

Temperature: 150 °C

Procedure

Sodium hydride (60%, 0.080 g) was added to ethylene glycol (3 ml) and the resulting suspension stirred under an atmosphere of nitrogen for 30 minutes. To this mixture was added a solution of N-(1-adamantylmethyl)-2-bromo-5-chloroisonicotinamide (Example 1(ii)) (0.192 g) in anhydrous N-methyl-2-pyrrolidinone (1 ml). The stirring bar was removed and the resulting solution heated in a MARS microwave for 15 minutes (300 Watts, 150° C.). The mixture was cooled and poured into water (50 ml) and extracted into is ethyl acetate (3×10 ml). The combined organic extracts were washed with brine (2×10 ml), dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by chromatography on silica gel eluting with ethyl acetate:isohexane (1:1) to afford the sub-titled compound (0.092 g) as a white solid.

Workup

customThe stirring bar was removed
temperatureThe mixture was cooled
additionpoured into water (50 ml)
extractionextracted
washThe combined organic extracts were washed with brine (2×10 ml)
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified by chromatography on silica gel eluting with ethyl acetate:isohexane (1:1)

Sources & evidence

ORD record: ord-779672bb9afd47edbab7b0d1d89b13c8
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07129246B2

Reaction notes

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